Capital Wealth
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Fall Books · Literary life · Career

Washington Irving Sailed in 1815 to Save the Family Import Business. It Failed, and He Wrote Sleepy Hollow Instead

America's first literary star, the reviewer calls him. He made writing his living by accident, after a family business failed. Of a whole shelf of books, two short stories are what lasted.

By Sean Anees Saifi · Capital Wealth · Published Sunday, October 11, 2026 · Source: The Wall Street Journal, October 10–11, 2026 weekend edition, whose market figures are the Friday, October 9 close (Fall Books)
Key Points
1815
the year he sailed to rescue the family import business, which failed
17
years he then stayed abroad, by the review's count
19
his age when his first comic letters ran in a New York paper
$28.95
list price of Lopate's 288-page appreciation (Princeton)
A covered wooden bridge crosses a misty stream in bare autumn woods at dusk, with one lit lantern at its entrance and fallen leaves on the path.
Four biographies, several travel books and volumes of sketches go unread. Two short stories are what still get read.
In one line: Irving began writing for a living after the family import business failed in 1815. Of everything he wrote, two short stories are what lasted.

It's October. Somewhere near you a headless horseman is riding across a front lawn. The man who put him there, Washington Irving, didn't set out to write for a living. In 1815 he sailed abroad to try to save his family's import business. The business couldn't be saved. The book he finished in England sold so well that he decided to make writing his trade. Micah Mattix tells the story in the Journal's Fall Books section, reviewing Phillip Lopate's A Washington Irving Sketch Book (Princeton, 288 pages, $28.95).

Irving was America's first literary star, the reviewer writes. His spoof A History of New York came out in 1809 under the pen name Diedrich Knickerbocker. It was a hit at once and went through three editions in 10 years. Lord Byron told a friend, “His writings are my delight.” Walter Scott compared him to Swift. The pen name stuck to the whole city. New Yorkers are still Knickerbockers.

He was born in New York City on April 3, 1783, into a big middle-class family, and named for George Washington. His father was a merchant and a strict church deacon. A classmate remembered a shy, slow pupil. At 19 he published comic letters in a city paper his brother edited. In 1804 he went to Europe for his health and, his family hoped, his education. He came back in 1806 and put out 20 issues of a satirical magazine before the Knickerbocker book.

The fallback that became the career

Then came 1815 and the failed rescue of the family import business. He stayed abroad 17 years. In England he finished The Sketch Book of Geoffrey Crayon, Gent., the collection that holds Rip Van Winkle and Ichabod Crane. Both were drawn partly from Hudson Valley legends. Its success settled the question. He'd write for a living. Some readers back home thought its fond view of English country life was a betrayal, so soon after the War of 1812. He came home in 1832 anyway and wrote up a trip to the West. He never married. His fiancée, Matilda Hoffman, died at 17.

Lopate's book is an appreciation, the reviewer says, and it quotes at length. That pads a slim volume. It also puts the best of Irving in front of you directly. For the full life, fuller biographies exist. For the case that he's worth reading again, this one does the job.

Our read

This is Career, with a side of Estate, the legacy part. Two things in this story are worth a minute. First, the writing life started as the fallback. He was already famous for one book, but the family business was the plan. Writing for a living was what he did when the plan failed. Plenty of good working lives begin that way. It's worth building a plan that can survive the first plan failing. Second, look at what lasted. Four biographies, travel books, volumes of sketches, and the hit that made him famous. Almost none of it is read. Two short stories carry the name.

A legacy is rarely the part its owner expected. That's true of books, and it's true of estates. The thing your grandchildren keep may not be the thing you spent the most on. So the plan should be clear about what matters, in writing, while you're the one deciding. The umbrella gets bought on a dry day.

What It Means For Your Portfolio

Hold. Plan for the fallback, and name what should last

No portfolio action. Careers and legacies rarely go the way the owner planned, so the plan should survive a first failure and say in writing what matters.

General planning principles, not advice for anyone in particular. Keep a cash cushion big enough that a failed venture doesn't take the household down with it. By the review's dates, Irving had a few years abroad to find his footing. Most households get a few months.

On the estate side, write down which things carry the family's story, and who should have them. The valuable item and the meaningful one are often not the same.

Book a 15-Minute Review → Back to Edition No. 183 →